Cu-catalyzed asymmetric 1,4-addition of Me3Al to nitroalkenes. Synthesis of (+)-Ibuprofen

Polet, Damien; Alexakis, Alexandre

doi:10.1016/j.tetlet.2005.01.007

Article scientifique

Lettre

Anglais

Cu-catalyzed asymmetric 1,4-addition of Me3Al to nitroalkenes. Synthesis of (+)-Ibuprofen

Contributeurs/tricesPolet, Damien; Alexakis, Alexandre

Publié dansTetrahedron letters, vol. 46, no. 9, p. 1529-1532

Date de publication2005

Résumé

Trimethylaluminium undergoes enantioselective (ee up to 93%) copper-catalysed Michael addition to various nitroalkenes. Copper thiophenecarboxylate (CuTC) (2 mol %) and 4 mol % of a chiral phosphoramidite ligand are sufficient for a complete and clean reaction. The synthesis of (+)-ibuprofen is described with 82% ee.

Mots-clés

Copper
Aluminium
Nitro
Conjugate addition
Asymmetry
Ibuprofen

Structure d'affiliation

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (format ISO)

POLET, Damien, ALEXAKIS, Alexandre. Cu-catalyzed asymmetric 1,4-addition of Me3Al to nitroalkenes. Synthesis of (+)-Ibuprofen. In: Tetrahedron letters, 2005, vol. 46, n° 9, p. 1529–1532. doi: 10.1016/j.tetlet.2005.01.007

Article (Published version)

Identifiants

PID : unige:8123
DOI : 10.1016/j.tetlet.2005.01.007

ISSN du journal0040-4039

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Création21.06.2010 14:16:33

Première validation21.06.2010 14:16:33

Heure de mise à jour14.03.2023 15:48:13

Changement de statut14.03.2023 15:48:13

Dernière indexation15.01.2024 20:27:45

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Cu-catalyzed asymmetric 1,4-addition of Me3Al to nitroalkenes. Synthesis of (+)-Ibuprofen

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